Have I done it yet?

Have I overshared?

I was right to include the disclaimer in Monday’s blog post.  I warned you that this series would contain the most personal, intimate details that I have shared on TRB in twenty years of writing, but trust me when I say that it only gets more personal from here…

Nobody warned me about how hard it is to be middle-aged.  I mean, there are about a million movies, television shows, and books about it, so perhaps I had my fair chance to prepare, but I guess when it comes to growing older with your parents and siblings, there’s just no way to understand what’s coming.

My brother is a very private person.  I’m not sure that he would necessarily approve of my sharing this story in fantastic detail.

My sister is the complete opposite.  I could take out a billboard at Yonge & Dundas Square with my mother’s face on it, and she would not only approve, but applaud.

And then, stuck in the middle, is me.  The middle child, in case that wasn’t painfully obvious already.

Can any of you relate?  Any middle-children out there who can share some pearls of wisdom?

When I first proposed the idea of my mother moving from Scarborough back to Leaside during the onset of the pandemic in 2020, I didn’t think my mom would like the idea.  I was right, as it turned out, since she didn’t like the idea, but rather she loved it.

The very first question I asked my mother was, “Are you thinking a house or are you thinking a condo?”

My mother, the former school teacher, seemed to want to check all her boxes, so she said, “I’m open to considering both.”

I sent her a list of all the condos in Leaside, most of which are on Randolph Road or Millwood Road, and were built in the 1980’s or 1990’s.

There’s a lot to like about these buildings.  They’re all low-rise, usually 4-5 storeys, the layouts are generous compared to modern condos, and while Millwood Road is a busier street, they’re close to Trace Manes Park and the Leaside Library.

In the summer of 2020, I took my mother to see a condo at 211 Randolph Road.

It was a 2-bedroom, den, 2-bathroom layout, just under 1,000 square feet, with parking, a locker, and a small balcony.

This would be the first time I could see my mother in action and watch the proverbial hamster run on the wheel in her head.

She came into the unit with a very open mind.  She made suggestions about where she could put furniture, told me the features that she liked, and spent a fair amount of time in the unit.

But then seemingly out of nowhere, she simply looked at me and concluded, “You know, Dave, this is not the place for me.”

The next day, she called me to explain.

My mother is an outdoors person.  She spends hours each day sitting on her front porch and watching the world go by, as well as sitting on her back porch listening to the radio and reading the newspaper.  That back porch is also a focal point of every Sunday visit with her family (my children and I), as is the backyard for the kids to play.

One might suggest that she needs to look to the future, when the children are older and won’t want to play outside.  But having been through this process, I can tell you that this is a mistake.  “Live for now,” not for later.  Yes, you want to future-proof your downsizing option and “age in place,” but why deprive yourself of the largest joys in your life for today and tomorrow, just to make it a bit easier down the line?

My mom explained, “I don’t want to live in a condo.”

It was a hard stop.

Here’s where one percent of you might sarcastically say, “Oh, how nice for her,” but I don’t think the Paul Kershaw loyalists read TRB all that often, so maybe you’ll just support her decision and financial options, and wish her all the best.

My mom said, “That condo did have a balcony, but it could barely fit a chair and a table.  And so many condos in that building and others like it don’t have any outdoor space.  That’s not the life I want.”

Before I could offer her any insight, she said:

“I’d rather grow old and die in my house.”

It was so matter-of-fact.  Only a person her age could pull that off.

We decided to switch our focus to houses within the area, but with that, we entered a whole other arena of issues…

My mother said, “My dream would be to get a cute little bungalow.”

Oh boy.

That idea sounds great in theory, but do you know who else likes to buy cute little bungalows?

Developers.

The intrinsic value of a bungalow in Leaside is based on potential, not what’s actually present within the home itself.  So if you’re somebody who wants to buy the bungalow because you want a 2-bedroom, 2-bathroom house on a single level, then you’re going to value it at a lower price than the market will actually bear in response to what developers will pay before they construct a new McMansion on site.

I took my mother to see a small bungalow at the corner of Vanderhoof and Sutherland:

This time, however, my mother meant business!

For those of you who are of my vintage, do you remember Duotangs?

Remember back in school when you didn’t want a thick, plastic binder but wanted something to protect your notes?

My mother showed up with an orange Duotang tucked under her arm, and a pen in hand.  When we got inside the house, she placed the folder down on the counter, and I could see the sticker on the front that read “NEW HOUSE.”

Boom.  We were in business.

My mother then pulled out a measuring tape, took note of the length and width in the living room, and looked up at me while gritting her teeth.

“Dave, I don’t think my couch is going to fit here,” she said.

Now she was being like every other client!

“Mom, you don’t buy a house based on the size of your existing couch,” I told her.  But she responded, “I don’t want to get a new couch, though.”

This house needed work, but that wasn’t the actual problem.

The problem was the layout.

For those of you who are familiar with Leaside bungalows, or any bungalow, for that matter, you’ll know that the two bedrooms are at the back of the house.  Some of the layouts feature a sliding door in the second bedroom that opens to the backyard, but many of the layouts feature two bedrooms merely with windows, and thus, you can’t access the backyard from inside the house.

This was one such house, and the only way to the yard was to go out the side door, walk on the sidewalk, over the driveway, and through the back gate.

That proved to be a deal-breaker for my mother, who spends all her time in the backyard.  She was also thinking of her grandchildren, and didn’t want them walking on the sidewalk to get to the yard.  It was just inconvenient.  It lacked functionality.  It didn’t compare at all to what she had in her own house, where she could see the kids play in the yard from the kitchen.

We started to think that a smaller, 2-storey house would bridge the gap between what she had and what she wanted, and that maybe a 2-bedroom semi-detached would fit the bill.

I took her to see a house on Rumsey Road that was a 2-bedroom, 2-bathroom, semi-detached, on a smaller lot, which didn’t need much work.

The kitchen walked out to the back deck, which was exactly what she wanted.

The bedrooms on the second level were generous.

The basement rec-room was big, and had a high ceiling too!  This was another crucial element, since my mother’s current house had a massive basement that was filled with Lego, Barbie, doll houses, and even cars, trucks, and action figures that my mother was saving “just in case” there was a grandson.

But we soon discovered yet another deal-breaker.

My mother stood at the top of the stairs that led to the basement and just stared.

“Dave, I don’t know if I can do this,” she said.  Do…..what, exactly?

“You can’t get down the stairs?” I asked her, rather confused.  She lived in a 2-storey house right now, with multiple staircases.

My mom clarified, “No, I mean I don’t know if I can work with a single, tall staircase when I’m aging,” she said.

She then showed her sense of humour again when she said, “I want an L-shaped staircase, like what I have at my house now.  That way, when I eventually get old and fall down, I’ll only tumble down five stairs instead of ten.”

I mean, you can’t argue with that logic, can you?

It’s true, though; at her current house, she had a staircase going from the main floor to the second, and a staircase going from the main floor to the basement, both of which were L-shaped and extra-wide.

“This staircase is a death sentence for an 80-year-old,” my mother said.

And with that, another option for us was pooched.

In the fall of 2020, I went to see a house on Randolph Road, about one block from Rolph Road Public School, that I thought could be a great fit for my mother.  It was a 3-bedroom, 2-bathroom, semi-detached that did have an L-shaped staircase to the basement!  It was upgraded, there was a private driveway, and it seemed to be the perfect fit.

But it was priced at $1,500,000, however, and that’s just not something I thought we could afford.

This is why I didn’t take my mother to see the house, even though I felt it was something that would work for her.

Surprisingly, the property sat on the market throughout the fall and was eventually reduced in price to $1,479,000, then $1,449,000.

I started to wonder if this is something that could fall into our laps?

Christmas rolled around, and with the holidays comes a lot of time with family.  It became more apparent that our whole family would benefit from my mother moving to the midtown area, and so I decided that when the new year began, I would push the search a little harder.

New listings were scarce in early 2021, so I eventually went back to the agent who had listed the semi-detached house on Randolph.

The house was last listed for $1,449,000 and didn’t sell.  So what did that mean it was “worth?”  Maybe $1,400,000?  Would the sellers take $1,375,000?  Since I’m a licensed agent, I would get a 2.5% real estate fee on the buy-side, which I could use to reduce the purchase price.  Could I net this thing out at something like $1,335,000?

In February of 2021, I called the agent and asked, “Hey, those folks you’ve got on Randolph.  Any chance they’re still interested in selling?”

The agent chuckled.  I figured his response could go either way.

“Do you have any idea how many agents have called me about that house?” he asked.

It seemed that it was going the wrong way…

“Since the first of January, I’ve had calls on that house.  The market has completely changed from last fall.  Anyway, I sold it a few weeks ago.  We got a great price!”

I was crushed.

But the irony is, I hadn’t even told my mother about the house!

That weekend, during our regular Sunday visit, I told my mom that I had the perfect house for her, but we missed it.  The timing was wrong.  The price was too high.  I just couldn’t believe that the opportunity was there, and I failed to seize it.

My mom didn’t really react.

I continued to regale her with my feelings of doubt, regret, and guilt, but she just sat quietly.

I kind of felt like she was holding something back, and this feeling was confirmed when she dropped this bombshell on me:

“Dave, I’ve been thinking about it, and I don’t think I want to move anymore.”

Mic……drop.

I was beyond surprised.  I was shocked.

She said, “The more I think about it, the more I like my house!  I want my computer room.  I want my sewing room.  I love that the kids can play with toys in one area of the basement and do art in the other.  I just……I just……I just really like my house.”

She went on to describe the features of her house with such incredible passion that I almost began to wonder why we thought about her moving in the first place.

By the time she was finished with her soliloquy, I was sold on the idea of her staying put in the only house she had known for nearly two decades, which is the longest she had stayed in any dwelling during the course of her life.

As many of you will recall, 2021 was a crazy year in the real estate market.  I watched first-hand as prices in Leaside skyrocketed, and suddenly those $1,450,000 semi-detached houses were worth $1,800,000.

At the high point, there were two semi-detached houses on Randolph Road, both with main-floor family room extensions, that sold for $2,100,000.

By early-2022, we were in peak insanity.  Those $1,400,000 bungalows were selling for over $2,000,000 to builders who wanted to sell their finished products for over $4,000,000.

The market slowed down in mid-2022, then began its decline, but it still didn’t stop me from wondering, “What could have been?”

But my mother was happy!  That’s what was important!

By the summer of 2022, we didn’t even discuss the potential of downsizing any longer.  We were two years from the start of COVID, and things were starting to normalize.  My son was now over two-years-old and my daughter would be six-years-old in the fall.  We enjoyed my mom’s backyard all summer long, barbecued every Sunday night, and she even spent some time upgrading the house a little.  Nothing major, but a few new light fixtures here, a new coat of paint there, and it seemed she was planting deeper roots than ever before.

We turned the page to 2023 and then eventually to 2024.

Occasionally, a friend or colleague would ask, “Hey, whatever happened to the idea of moving your mom?” to which I would respond that my mother had decided that she wanted to stay put.

As I shared on my blog in 2024, I purchased a couple of condos for long-term investments, perhaps repositioning some of the funds that I might have used to buy a house for my mother if things had gone that way.

By the spring of 2025, it occurred to me that it had been five years since my mother had her brief dalliance with downsizing.  I can’t remember the exact moment, and maybe it was in the summer of 2025, but I told my mother that she should consider replacing a piece of furniture in the house that was looking a little worn.

That’s when she dropped this little nugget:

“Well, I wouldn’t want to buy anything new that wouldn’t fit with a property, you know, whenever I downsize…”

You don’t say?

She didn’t elaborate, and I didn’t ask her to, but it was clear that the idea was somewhere in her mind.

In the fall of 2025, a listing in Leaside caught my eye.

It was a detached bungalow on a deep lot, but unlike the bungalows that we had considered previously, this one was only a one-bedroom.

You might ask, “Who the hell wants a one-bedroom house?”

The answer would be: maybe my mother?

There were originally two bedrooms, don’t get me wrong, and the second bedroom had a sliding glass door that led out to a massive two-tier deck, under a tree canopy.  But the owners had opened up the walls to combine the primary bedroom with the second bedroom, and thus, the area where the second bedroom was located was essentially a walk-through hallway to the yard.

It was priced at $1,500,000, however, so I didn’t give it much more thought after my initial, “Huh, this could work…”

A few months later, the property was reduced to $1,479,000, and then to $1,449,000.

I had it saved in my “favourites” but I still really wasn’t thinking about it as an option.

The property finished the year on the market at $1,429,000, and we turned the page to 2026.

In January, the property was re-listed for $1,419,000, which I thought was kind of funny, because it reeked of a seller who didn’t want to reduce, but knew she had to.  Let’s face it: a $10,000 reduction doesn’t move the needle, and is barely even what you’d consider “symbolic.”

Now you might ask: why wasn’t this property selling?

First and foremost, while this was a bungalow and a potential target for developers, most developers had stopped doing “spec-builds” in 2024 or 2025.  They were looking to build for end-user clients and not take the risk associated with building a $3.5 – $4M property to sell in 2026 or 2027.

But I will also admit that the house was located on the first block in from a very busy street, which would also deter developers, and it backed onto a low-rise condominium.  Some buyers wouldn’t be bothered by this in the slightest (aka, my mother), but this was all the more reason for developers to avoid the lot.

Not only that, the one-bedroom nature of the home had diminished the buyer pool.  Sure, a buyer could easily put a wall back up, but even then, how many people are looking for 1940’s, 2-bedroom bungalows, with dated finishes, and in “C-” condition at best?

The page turned to February, and our business began to ramp up.  I hadn’t thought of the house for several weeks.

Then one day, I received an email from my mother.

Subject Line:

“There’s a house I want to see.”

I wondered which house this could possibly be!  Where was it?  Different location?  Or close to us?

You wouldn’t believe it.

Or maybe you would?

It was the same house I had bookmarked months prior and was patiently watching…

(TO BE CONTINUED)